overseer-plan_skill

Overview

This skill converts Markdown planning documents into tracked Overseer tasks using MCP codemode. It reads a plan or spec, extracts the top-level title as a milestone, analyzes heading structure to produce tasks and subtasks, and persists them into Overseer. The output includes created task IDs and a concise breakdown summary for review and iteration.

How this skill works

The skill parses the Markdown file, uses the first H1 (stripping a "Plan: " prefix if present) as the milestone title, and inspects headings and lists to derive child tasks (depth 1) and subtasks (depth 2). It enforces task quality rules (atomic, validated, clear), applies priority and optional parent linking, and calls the Overseer MCP codemode to create records in SQLite. After creation it returns IDs and supports later operations like get, list, start, and complete.

When to use it

• After finalizing a plan in plan mode and you need tracked work items
• Converting specs or design docs into implementation task hierarchies
• Turning roadmap or milestone documents into assignable tasks
• Preparing work for sprint planning or handoff to engineers
• When you want systematic, testable acceptance criteria attached to tasks

Best practices

• Keep sections focused so the parser yields atomic tasks (one committable change each)
• Include explicit acceptance criteria or "Done when:" lines for validation
• Structure documents with clear H1/H2/H3 headings to control milestone/task/subtask depth
• Set priority 1-5 and use --parent only when nesting under an existing Overseer task
• Run the Oracle review step to iterate on the proposed breakdown before persisting

Example use cases

• Convert a design doc into a milestone with implementation tasks and tests
• Create a sprint backlog from a roadmap markdown file with priorities
• Break a feature spec into tasks and subtasks for frontend, backend, and infra work
• Import a migration plan and attach explicit acceptance criteria to each task
• Turn a cross-repo implementation guide into an Overseer milestone with tracked children